2715-70-0Relevant academic research and scientific papers
Synthesis and crystal structures of fluorescent receptors for 9-butyladenine
Lamale, Bassam,Henry, William P.,Daniels, Lee M.,Zhang, Cungen,Klein, Suzane M.,Jiang, Yu Lin
, p. 62 - 69 (2009)
Two pyrene containing fluorescent receptors, 2-(1-pyrenyl)benzoic acid (FR-1) and 8-(1-pyrenyl)-1-naphthoic acid (FR-2), have been designed and synthesized to mimic a pyrene dinucleotide for molecular recognition of 9-butyladenine (9-BuA). The X-ray cryst
Poly(ethylene glycol)-based ammonium ionenes containing nucleobases
Tamami, Mana,Hemp, Sean T.,Zhang, Keren,Zhang, Mingqiang,Moore, Robert B.,Long, Timothy E.
, p. 1588 - 1595 (2013)
Adenine-functionalized ionenes (ionene-A) and thymine-functionalized ionenes (ionene-T) were synthesized from novel nucleobase-containing monomers from an efficient aza-Michael addition to an acrylate precursor. Complexes of ionenes with nucleobase-containing guest molecules (n-butyl thymine, nBT and n-butyl adenine, nBA) exhibited well-defined complementary hydrogen bonding interactions. Job's analysis revealed a 1:1 stoichiometry for the hydrogen-bonded complexes of [ionene-A]:[nBT], [ionene-T]:[nBA], and [nBA]:[nBT]. A mathematical fit of the chemical shifts to the Benesi-Hildebrand method revealed the association constants of 94 M-1, 130 M -1, and 137 M-1 for complexes of [ionene-A]:[nBT], [ionene-T]:[nBA], and [nBA]:[nBT], respectively. Furthermore, DSC thermograms of 1:1 [ionene-A/T]:[guest molecule] complexes showed the disappearance of the melting transition for the guest molecule, confirming the absence of macrophase separation of the nucleobase guest in the polymer matrix. Morphological studies including atomic force microscopy (AFM) and small-angle X-ray scattering (SAXS) revealed a microphase-separated morphology for the nucleobase-containing ionenes and less defined microphase separation for the 1:1 complexes.
Adenine-based urea receptors in fluorescent recognition of iodide
Ghosh, Kumaresh,Sen, Tanushree
, p. 7204 - 7208 (2008)
Adenine-based receptors 1 and 2 are designed and synthesized for selective sensing of iodide over the other halides and carboxylate anions. Both the receptors 1 and 2 use the urea motif for binding carboxylates and halides. Emissions of the naphthalene and the anthracene in 1 and 2, respectively, are monitored in CHCl3 in detecting the anions. While carboxylates, fluoride, chloride, and bromide increase the emissions of naphthalene and anthracene in both the receptors 1 and 2 during complexation, iodide quenches the emission. Such selective quenching allows iodide to be discriminated from other halides and carboxylate anions.
Adenine-based receptor for dicarboxylic acids
Ghosh, Kumaresh,Sen, Tanushree,Fr?hlich, Roland
, p. 7022 - 7026 (2007)
The adenine-based fluorescent receptor 1 was designed and synthesized for the selective recognition of dicarboxylic acids in CH3CN. The recognition takes place through the Hoogsteen binding site of adenine with concomitant PET quenching of the anthracene moiety. The carboxylic acid binding to 1 was investigated by 1H NMR, X-ray, UV-vis, and fluorescence spectroscopic methods. The Hoogsteen (HG) cleft of receptor 1 is found to be selective for glutaric acid.
A new 9-alkyladenine-cyclic methylglyoxal diadduct activates wt- and F508del-cystic fibrosis transmembrane conductance regulator (CFTR) in vitro and in vivo
Boucherle, Benjamin,Bertrand, Johanna,Maurin, Bruno,Renard, Brice-Lo?c,Fortuné, Antoine,Tremblier, Brice,Becq, Frédéric,Norez, Caroline,Décout, Jean-Luc
, p. 455 - 465 (2014/07/21)
Cystic fibrosis transmembrane conductance regulator (CFTR) is the main chloride channel present in the apical membrane of epithelial cells and the F508 deletion (F508del-CFTR) in the CF gene is the most common cystic fibrosis-causing mutation. In the sear
Anthracene coupled adenine for the selective sensing of copper ions
Ghosh, Kumaresh,Sen, Tanushree
scheme or table, (2010/08/19)
Anthracene-based adenines 1 and 2 have been designed and synthesized, and their metal ion recognition properties have been established fluorometrically. Both molecules exhibit Cu 2+ induced ON-OFF type signaling patterns over the other representative metal ions studied. Compound 1 exhibits 97% quenching of emission in the presence of Cu 2+ whilst derivative 2 shows 81% quenching under similar experimental conditions.
8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
Lambertucci, Catia,Antonini, Ippolito,Buccioni, Michela,Dal Ben, Diego,Kachare, Dhuldeo D.,Volpini, Rosaria,Klotz, Karl-Norbert,Cristalli, Gloria
experimental part, p. 2812 - 2822 (2009/09/08)
Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio
Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid
Klein, Suzane M.,Zhang, Cungen,Jiang, Yu Lin
, p. 2638 - 2641 (2008/09/19)
A simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid (HI) is reported. The alkyl iodides were obtained in quick and easy work-up with good to excellent yields (66-94%) and very high purities (97-99%). Freshly prepared iodomethane and 1-iodobutane were applied to synthesize biologically relevant 3,7-dimethyladenine and 9-butyladenine, which were characterized thoroughly using 1D and 2D NMR, individually.
7′-Substituted benzothiazolothio- and pyridinothiazolothio-purines as potent heat shock protein 90 inhibitors
Zhang, Lin,Fan, Junhua,Vu, Khang,Hong, Kevin,Le Brazidec, Jean-Yves,Shi, Jiandong,Biamonte, Marco,Busch, David J.,Lough, Rachel E.,Grecko, Roy,Ran, Yingqing,Sensintaffar, John L.,Kamal, Adeela,Lundgren, Karen,Burrows, Francis J.,Mansfield, Robert,Timony, Gregg A.,Ulm, Edgar H.,Kasibhatla, Srinivas R.,Boehm, Marcus F.
, p. 5352 - 5362 (2007/10/03)
We report on the discovery of benzo- and pyridinothiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7′-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chloro-benzothiazol-2-ylsulfanyl)-9-(2-cyclopropylamino-ethyl) -9H-purin-6-ylamine).
Molecular recognition in micelles: The roles of hydrogen bonding and hydrophobicity in adenine-thymine base-pairing in SDS micelles
Nowick, James S.,Chen, Jenny S.,Noronha, Glenn
, p. 7636 - 7644 (2007/10/02)
This paper describes a new class of molecular receptors 2 that bind adenine derivatives 3 in aqueous solution by means of hydrogen bonding (base-pairing). The receptors are supramolecular assemblies of thymine groups embedded in micelles, which self-assemble when (thyminylalkyl)ammonium salts 1 [Thy-(CH2)n-N+Me3] are mixed with aqueous sodium dodecyl sulfate (SDS) solutions. NMR titration studies and Job's method indicate that binding occurs with 1:1 adenine-thymine stoichiometry in a fashion consistent with base-pairing within the micelles. In the absence of SDS, base-stacking occurs in preference to base-pairing. Three factors that were anticipated to be most significant in binding were examined: the lipophilicity of the adenine substrate, the position of the thymine group within the micelles, and the role of SDS in binding. To study these factors, the length of the alkyl group on adenine 3 (m = 1, 2, 3, and 4), the length of the alkylammonium chain of thymine 1 (n = 4, 6, 8, and 10), and the concentration of SDS (0-40 mM) were varied. The lipophilicity of the adenines was found to have the greatest effect upon the measured association constant Kobs. A binding model is proposed in which adenine 3 first partitions between the bulk aqueous solution and the interior of the micelle and then base-pairs to the thymine group within the micelle. In accordance with this model, a linear relationship is observed between log Kobs and log Kow (where Kow is the octanol-water partition coefficient of adenine 3).
